


anthony's obvious crossdressing kink

by extremelyquestionable (TechnicalTragedy)



Category: The Derp Crew (Youtube RPF)
Genre: Begging, Consensual Somnophilia, Crossdressing Kink, Dom/sub Undertones, M/M, Masturbation, RoyalChaos, ZeRoyalChaos
Language: English
Status: Completed
Published: 2014-12-03
Updated: 2014-12-03
Packaged: 2018-02-27 23:34:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,312
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2710781
Author URL: https://archiveofourown.org/users/TechnicalTragedy/pseuds/extremelyquestionable
Summary: <blockquote class="userstuff">
              <p>Anthony wears a dress, might be a narcissist, and his fingers are not enough. Steven has what he needs.</p>
            </blockquote>





	anthony's obvious crossdressing kink

Anthony swallows hard, eyes tightly closed. This was a dumb idea. This was a really, really dumb idea. It’s especially dumb to do this now, since Steven could come back at any minute and it would be horrifyingly embarrassing to be caught like this. Though apparently his dick thinks that’s a great idea, since he can feel himself getting hard beneath the soft dress he’s got on. His breath catches in his throat as the new texture meets his cock, and, without his knowledge, he bites his lip nearly hard enough to draw blood. This was a bad, bad idea.

Anthony isn’t sure what made him decide to put on the dress that had been gathering dust in the very back of his closet, but he’s cursing that thing. The dress is dark pink, almost red, and cut low in the back, with a short skirt. He’s always liked feeling the texture of the dress, liked the slippery, silky feel of it between his fingertips. Somewhere along the line that must’ve translated into wanting to have that feeling all over his body. That want had only recently manifested itself, and it had done so at a very inopportune time. Namely, the moment Steven stepped out of their small shared apartment to go run some errands, due to be back in an hour or so. And Anthony, because he had trouble with self-control, had thrown the dress on and then spent nearly half an hour with his eyes closed, worried about seeing himself in a dress.

Oh god, Steven. He could literally walk in at any second and see Anthony standing there in a dress with an obvious hard-on. For some reason, the thought of that made Anthony’s cock jump again. He didn’t want to think about what that meant.

Taking a deep breath, Anthony pries his eyes open and looks at himself in the full-length mirror propped against the living room wall. His eyes widen as he sees himself, and he thinks maybe he’s developing a serious case of narcissism. He looks really good in this dress. He runs his hands down his sides, liking the way it feels to have the heat of his fingers replace the coolness of the dress. He makes a face at his legs, briefly wondering if he should’ve shaved them, before deciding that that might be taking it a bit too far.

Anthony plays around with the dress a bit more, showing himself off in the mirror and ghosting his fingers over his skin. His dick is nearly forgotten until he brushes over his nipples, sending a new wave of arousal washing through him and bringing his attention back to the tent at the front of his dress.

He looks down at himself for a long moment, before smoothing his hands down his chest and massaging at his thighs. Anthony watches his hands move in the mirror, until the anticipation he’s building up starts to make his cock throb. He palms the head of his dick, and a wet spot quickly forms on the dress. Anthony feels a blush stain his cheeks as he stares at the dark patch.

He feels naughty, like he’s taken a cookie from the cookie jar and hasn’t been caught for it yet, and it’s spectacular.

Anthony hesitantly wraps a hand around his cock, bringing the fabric of the dress with him and rubbing it up and down his shaft. He lets out a quiet noise, biting down on his lip again. He pumps himself a few times, the silky dress still gathered in his hand as he does so, but pretty soon he feels like he might come if he keeps it up. Though his restraint may be shit, he does want to keep his dress nice.

Anthony releases his dick and the silk falls back into place, slightly wrinkled now. A thought occurs to him, and his blush darkens to a deep scarlet. Could he- No, no, that’s too much. Anthony may put on dresses and maybe have wet dreams about his male best friend sometimes, but sticking fingers up his ass is way too gay. The temptation feels stronger than he is, though. The idea is in his head, and he really wants to try it, since he’s never “gone all the way” before.

Anthony gnaws on his lip, unable to take his eyes off of the side table where he knows a bottle of lube is. He’s played with himself, but this is different. Like this is going to cross an invisible line drawn somewhere.

His mind is made up before he knows it is, and he finds himself settling his knees on the couch cushions and leaning against the back with the lube in one hand and the hem of his dress in the other.

Anthony hikes the skirt of the dress up above the swell if his ass and then goes about opening up the lube. He pops open the bottle and drizzles some on his fingers. It’s cold, too cold, so Anthony rubs it between his fingers, trying to warm it up. When he feels like the lube isn’t made of ice anymore, he gathers the hem of his dress in his hands again and pulls it a little higher so it won’t be in the way.

Anthony reaches back and circles his entrance with a finger, clumsily teasing the rim by pressing in just a bit before backing off. After a minute or two of playing with his hole, he slides his index finger in to the first knuckle, giving himself a moment to adjust before pushing in steadily until his whole finger is inside the narrow channel. Anthony lets out a breath he didn’t know he was holding, and carefully wiggles his finger around to see if there’s enough room for another. He tries to stretch himself out as much as possible before adding the second finger, but he still winces at the slight burn. Eventually he gets two whole fingers in himself, and then a third slides home, too.

He fucks himself back on his fingers, but it’s at the wrong angle, his fingers aren’t long enough, and though occasionally he brushes a spot within himself that makes stars dance in front of his eyes, Anthony feels tears of frustration welling up in his eyes. He’d finally taken the plunge and indulged his most secret wants, and now he can’t even get the release he needs from it. He growls at himself, but it quickly turns into a half-sob when nothing comes of his pointless anger.

Anthony’s movements are just starting to slow down when the telltale sounds of someone unlocking the door to the apartment reach his ears. Horror grows in him as he realizes what that means. Steven’s home. Anthony is wearing a dress and finger-fucking himself on the couch. Steven will open the door and catch Anthony in the act. Anthony’s flagging erection springs back to life as these thoughts whirl through his head.

"What the fuck," Steven says, and Anthony startles, sending his fingers deep inside himself, deep enough to skate over his prostate.

Anthony lets out an embarrassingly loud moan, melting into the back of the couch. “Ste-e-e-e-ven,” he whines unintentionally.

"Anthony, what the fuck am I looking at? Are you … Are you in a dress? And your fingers- Oh god, what did I walk in on?" Steven half turns away, allowing Anthony a perfect view of the growing bulge in his jeans. The sight of it launches words out of his mouth.

"Fuck me," Anthony says, and Steven’s eyes fly back to him, eyebrows near his hairline and pupils blown wide.

"W-What?" Steven stuttered.

Anthony uselessly fucks himself on his fingers. “Steven, please. I can’t, it’s not, I need- Steven, please, please, please fuck me,” he begs, far past the point of caring.

"Oh fuck. This is fucked. Anthony, you don’t want-" Steven tries to say, but Anthony won’t let him finish, because if his wrecked-to-shit voice is any indication, he’s being worn down.

"Need you, Steven. Need you to fuck me. Don’t just want it, fuck, fuck, I need it. Need you, please, please," Anthony pumps his fingers in himself a couple more times, and when it has the same lack of effect as last time, the frustration finally boils over, sending tears tracking down his cheeks. "Fuck! Please, Steven, please!"

A war plays out on Steven’s face, but then it resolves into a tight smirk and he nods. “Since you asked so nicely.” He closes and locks the door behind him as he advances into the apartment, coming to stand right behind Anthony. “Remove your fingers,” he orders, and Anthony hurries to comply, bringing it up to join the other in clutching onto the frame of the couch. Anthony hears a piece of clothing hit the floor, and then the jangling of a belt being undone. His grip on the couch tightens in anticipation, and he can’t help the smile that spreads across his face.

Steven wraps a hand around his cock, stroking himself to full hardness, before reaching over for the lube. He opens the bottle and squirts a generous amount in his hand, before spreading it over his length. He presses himself against Anthony’s entrance, but not inside, not yet. He smiles as he says, “You really need this?”

Desperately afraid that Steven is having second thoughts, Anthony complies to the silent demand. “Yes, yes, yes, please fuck me, Steven. Please, please, I need it. I need you. I need your cock in me. Please, please fuck me.”

Grinning, Steven pushes into Anthony’s tight ass, rubbing his hips soothingly to try and distract him from the stretch. Anthony lets out a long whine once Steven is fully seated, already trying to rock his hips back and forth, but Steven’s hands on his hips anchor him. After allowing Anthony a short time to adjust, Steven slides back out until just the tip of his cock remains inside Anthony. He waits just long enough that Anthony starts to squirm, before slamming back into him and then out again, setting a brutal pace. Anthony can do nothing but hold on and moan as Steven fucks him hard, every thrust brushing over his prostate and sending him further and further out of his mind with pleasure.

"Look at this nice dress, Anthony. You like wearing dresses? They make you feel pretty? You look absolutely beautiful right now, you know that? You take my cock so well. Your hole is so open, probably wider than it’s ever been, huh? Ever been fucked before, Anthony?" When Steven doesn’t receive an answer, he halts all movement. "Gonna answer me?"

"Ungh," Anthony groans, wiggling his hips to try and get some friction going again.

"What was that, Anthony? Use your words."

"No, Steven. Never been fucked. Just you," Anthony forces out, and this time when he pushes back, Steven lets him seat himself fully on his cock again. Anthony makes a pleased sound, and starts rocking against Steven, fucking himself on his dick.

Steven smiles. “Just me? Have you ever let somebody see you in a pretty little dress like this before?”

Anthony shakes his head. “Just you,” he breathes, continuing his movements.

Steven leans down to press a kiss in between Anthony’s shoulder blades. “Want me to make you come?” he asks against Anthony’s heated skin.

The Italian moans and nods, so Steven slides his hands around from Anthony’s hips to his cock, one hand on his shaft and the other fondling his balls. Steven pushes his hips flush against Anthony’s ass, leaning up to bite at his neck. It’s awkward, but he feels it’s worth it when Anthony lets out a high-pitched whimper.

"Come for me," Steven whispers, and after another couple of strokes, Anthony does. Steven makes sure to cup his hand around Anthony’s dick so his jizz doesn’t get on the couch or the dress, and then he carefully maneuvers Anthony off the back of the couch and onto his back on the cushions.

Before Steven can make a decision about what to do with the quickly-cooling fluid on his hand, Anthony grabs his wrist and pulls it towards his face, licking Steven’s hand clean and pressing a sloppy kiss to the center of his palm. It simultaneously makes Steven’s heart and dick swell, and he’s reminded of his erection.

"Uh," he says intelligently, not as confident now as he’d been before, and wondering if he even needs to get off at all.

Anthony flicks his eyes down to Steven’s cock, and, after a moment of deliberation, divests himself of the dress, wiggling around to get it off and then draping it over the arm of the couch. He rolls over and presents his ass to Steven. “Keep fucking me,” he mumbles, “Gently. If I fall asleep, just keep going. Nothing personal, I’m just fucking exhausted.”

Steven considers it for a moment, but nods, moving into a better position. “You sure?”

Anthony is too tired to roll his eyes, so he just shifts his hips slightly up. “Dumbass.”

When Steven does come, it’s not the crashing wave he’s used to, but more of an exhale. He stumbles around, finding a cloth to clean himself and the sleeping Anthony up, before falling onto the couch beside the tall man, snuggling into his chest and haphazardly tossing a blanket over them.

Steven falls asleep wondering what waking up will bring. Will this have been the first and only time? Maybe something amazing will come of this, only to end and ruin their whole relationship. Perhaps this is just the start of a new chapter in their story, or some similarly sappy bullshit. Whatever happens, Steven’s just glad to be pressed close to someone he adores, and that Anthony finally gave in to his fucking obvious crossdressing kink.


End file.
